Hi Pirate - Your questions are reasonable and it sounds like you have your heart set on a fun adventure. As aspect to consider is the general on water experience of your group... 5-7 days can be fantastic and go by too quickly, or it can be miserable for those with uncontrollable sea sickness and seemingly linger on way too long. Although not a guarantee that y'all would be fine for a week, I would advice to ensure everyone has spent a bit of time on the water on any type of smaller vessel and perhaps experiment with a couple different types of sea sickness prevention meds or methods.

The expenses vary greatly as indicated by some of the responses above but can easily be $10K if going through the larger companies with overheads, middlemen, etc. In addition be sure to confirm that whatever Captain you secure is truly interested in being as much of a teacher as a skipper / person in charge of the vessel. It is a lot of responsibility for a skipper to sail an inexperienced group and even more work for him/her to teach along the way - so secure one that relishes the teaching aspect as that seems important to you.

I have a small private charter company with my one mono haul and will be booking charters in to / out of USVI (since I'm a US registered company) starting around March 2017 (I will likely be in the Windward Islands earlier in the season). PM me if you would like to chat more. My charters specialize in hands on teaching.

December will come before you know it, so good you are planning early. Booking fill up fast starting 6 months out.
I am not near as experienced as many on this forum, but here is my 2 cents.
First, not sure why you have decided on the Caribbean, but don't overlook the Bahamas and Coastal Southern Florida and the Keys as your first cruising vacation, especially if you are US citizens/residents. That alone will save you much time and money ( like thousands).
I have only chartered the big island of Hawaii, the BVI, the Bahamas (Nassau to Exumas), southern coastal Florida, and the Keys out to Dry Tortugas So far the Keys have been my favorite. Great sailing and snorkeling and pretty easy to get around on land, air and sea.
I will admit that I am now biased as I have started offering captained charters around coastal Florida and the Bahamas on my Leopard 46, 4 cabin Cat. December is wide open(:>)

My suggestion is Horizon Charters Grenada. I chartered from them during Easter 2014 and we sailed from Grenada to Bequia and then back slowly to Grenada taking in the Grenadines. They are a great bunch of people and have skilled skippers for hire. They know all the great snorkelling sites. Snorkelling and barbecues are a must. Do it man, just do it! Ask for Jacqui.

Generally, your best bang for the buck will be a privately owned and operated crewed or captain only yacht. In the BVI, a great place for an initial charter, these will almost all be members of the Charter Yacht Society of the BVI, and the website at bvicrewedyachts.com will give you an idea of what it's all about. These are the boats that participate in the Tortola Boat Show so they are generally in excellent condition and much better equipped than anything you will find at any of the charter companies, with toys, functional watermakers, bigger dinghies, you name it. They are generally a much better deal, as well. Most of these boats go out through charter brokers, but can be directly booked, as well. They are also legal and licensed and go through inspections, which is not the case with every boat you may run across. And a real advantage is that you know the boat you are going to charter and you know who the captain is going to be, and the chef, too, if there is one involved. At the big companies, you charter a boat (which may or may not be the one you actually get) and the skipper is not truly determined until right before the charter. It's the nature of the business....you don't know who your airline captain is going to be, either! But, the yachts I am talking about all have their specific live-aboard crews, so you can pick whom you want and begin to develop a relationship. Finally, some of these boats do instruction, either formally or informally, so you might be able to get a certification out of it, as well. For what you are looking to do, you could get a cat for around $6000, including skipper, plus operating expenses, or go up from there, as high as you want! 74 footer for $40,000? Higher still? But there are very good boats for small budgets, too. PM me if you need to know more... I operate a Leopard 45 at very competitive rates, and I teach.

Some companies rent a bare boat and chuck a skipper onboard so basically you decide where you are going. Some other companies run more of a structured cruise and their boats always come with a skipper and cook. They go on a pretty set route taking you to the best spots.
So determine what you want.

For a first time charter and first time sailors I would recommend the British Virgin Islands because they are beautiful, close together, protected from the worst ocean waves, good snorkeling, good testurants and good (or crappy depending on your tastes) nightime drunken activity.

Btw others have mentioned there is a hierarchy of companies from expensive to slightly less expensive. The most expensive have newer boats. That can be nice.

Thank you for all the replies - yes, even the little side-bar between American & Hoofsmit! :-0 I appreciate all the information & insights you all have. I know not every opinion will be the same - that's just fine. I like different perspectives!

I guess I should say that the Caribbean is not the only option...we love the Caribbean...been there a few times over the years & love the diving. Never been to BVI, but we would certainly be open to exploring other options...BVI, Florida Keys, etc. I am concerned, however, about the increased chances of cooler weather in FL that time of year. (Like I would have anything to complain about - I live in Indiana!!). But, if the cost would be a bit less, that is always attractive.

Our overall wants & needs is probably not foreign to anyone - we want a great vacation, learn as much as we can about sailing (maybe even get a certification?), enjoy the great benefits of sailing, go diving, snorkeling, fishing, sunning and of course some fun night life to cap it off. I'm sure everyone reading this knows where I'm coming from!!

Obviously, I have a lot of research to do, so keep the your thoughts coming!!

As an experienced charter captain in the Caribbean the first question I have is are you couples or single? That's a lot of people on a sailboat. Agree that a Cat is most likely your best option.

I have booked hundreds of learning cruises. Not a bad idea if all your crew are interested in learning but most captains are willing to allow you to sail and will share their knowledge. Read a good book on basic sailing before you go.

Do the BVI as your first entree to sailing in the Caribbean.

Personally I would bite the bullet and spend the bucks on a crewed charter with Voyage. Lot's of good suggestions above as well. They sent me an email recently with some great air fares.

Personally I can't imagine someone motoring to increase the gas bill on a sailboat. They don't burn that much but what do I know.

Personally I can't imagine someone motoring to increase the gas bill on a sailboat. They don't burn that much but what do I know.

Well, now that the majority of the world's charter captains have weighed in on the subject, we can scientifically reject the notion that any charter captain would ever do anything at all to take advantage of customers. In fact, based on the evidence presented, we should expect charter companies and their captains to secretly refill dieseltanks to offset the possibility of additional costs, then sneak into the customer's cabin at night, to replenish any cash spent ashore!

All of my previous experiences to the contrary were clearly hallucinations. I'm scheduling a scan ASAP. I probably have brain tumors.

My suggestion is Horizon Charters Grenada. I chartered from them during Easter 2014 and we sailed from Grenada to Bequia and then back slowly to Grenada taking in the Grenadines. They are a great bunch of people and have skilled skippers for hire. They know all the great snorkelling sites. Snorkelling and barbecues are a must. Do it man, just do it! Ask for Jacqui.

I have used every charter company in the Caribbean and Horizon is my favorite. One option is to charter with an instructor/captain.

Well, now that the majority of the world's charter captains have weighed in on the subject, we can scientifically reject the notion that any charter captain would ever do anything at all to take advantage of customers. In fact, based on the evidence presented, we should expect charter companies and their captains to secretly refill dieseltanks to offset the possibility of additional costs, then sneak into the customer's cabin at night, to replenish any cash spent ashore!

All of my previous experiences to the contrary were clearly hallucinations. I'm scheduling a scan ASAP. I probably have brain tumors.

Funny.
I laugh about the cost of diesel. How much fuel do you think a sailboat uses in a week especially with currentfuel costs? Honestly sorry you've had bad experiences. Recommend the scan right away.

Sailing in the BVI I would suggest will be a memorable Christmas. Chartering from owner (And almost all the boats in charter in BVI are owned individually by owners, and managed by Charter companies). I have ordered a Lagoon 42 which will be available by that time. If interested, PM me .

Hello Mr. Schaaf, I had previously contacted you about a year ago regarding seeking info about a BVI charter. Also, I recently sent you an email to that you suggested in a private message in which you sent (to your Jet Stream address). Anyway, I just wanted to make sure that address was still active. Please let me know...we are "still" wanting to plan a family vacation to the BVI for later this year. Thanks so much for your time!